Novel selective kappa-opioid ligands

Acta Crystallogr C. 1999 Mar 15:55 ( Pt 3):458-61. doi: 10.1107/s0108270198012736.

Abstract

The single-crystal X-ray structures of (-)-dimethyl[(2S)-1-(5,6,7,8- tetrahydro-5-oxonaphthalene-2-acetyl)piperidin-2-ylmethyl ]ammonium chloride, C20H29N2O2+.Cl-(BRL-53001A), and (-)-ethylmethyl[(2S)-1-(5,6,7,8-tetrahydro-5-oxonaphthalene- 2- acetyl)piperidin-2-ylmethyl]-ammonium chloride dihydrate, C21H31N2O2+.Cl-.2H2O (BRL-53188A), have been determined. The two molecules have different conformations in the 1-tetralon-6-ylacetyl residue but the same conformation in the 1-acetyl-2-(dialkylaminomethyl)piperidine moiety. The conformations found are in agreement with the required chemical features for kappa affinity and antinociceptive potency.

MeSH terms

  • Crystallography, X-Ray*
  • Ligands
  • Models, Molecular
  • Molecular Conformation
  • Piperidines / chemistry*
  • Receptors, Opioid, kappa / agonists*
  • Tetrahydronaphthalenes / chemistry*

Substances

  • BRL 53001A
  • BRL 53188A
  • Ligands
  • Piperidines
  • Receptors, Opioid, kappa
  • Tetrahydronaphthalenes